Question 1

Which of the following statements best describes the general properties of ethers?

Accepted Answer

Ethers are very stable and often used as solvents due to their unreactivity.

Question 2

Which reagent combination is used in the Williamson ether synthesis to produce an ether from an alcohol?

Accepted Answer

Alcohol and an alkyl halide with a strong base such as $\mathrm{NaH}$

Question 3

In the Williamson ether synthesis, which type of alkyl halide is preferred to avoid elimination side products?

Accepted Answer

Primary alkyl halide

Question 4

What is the major product when $\mathrm{RO^-}$ reacts with a tertiary alkyl halide under Williamson ether synthesis conditions?

Accepted Answer

An alkene via $\mathrm{E2}$ elimination

Question 5

Which of the following is a limitation of the Williamson ether synthesis?

Accepted Answer

It often leads to elimination products when using secondary or tertiary alkyl halides.

Question 6

Which mechanism is involved in the acid-catalyzed dehydration of alcohols to form ethers?

Accepted Answer

Formation of a carbocation intermediate followed by nucleophilic attack

Question 7

When synthesizing ethers via acid-catalyzed dehydration, which alcohols are most likely to react?

Accepted Answer

Secondary and tertiary alcohols

Question 8

What is the role of $\mathrm{H_2SO_4}$ in the acid-catalyzed formation of ethers from alcohols?

Accepted Answer

It protonates the alcohol, making it a better leaving group.

Question 9

Which of the following is true about the mechanism for acid-catalyzed ether formation from alcohols?

Accepted Answer

The nucleophile is usually another alcohol molecule.

Question 10

In the acid-catalyzed addition of alcohols to alkenes to form ethers, which intermediate is formed?

Accepted Answer

A carbocation

Question 11

Which of the following tips is NOT correct when drawing mechanisms for acid-catalyzed reactions?

Accepted Answer

The nucleophile is always a strong base.

Question 12

Which of the following reactions is called the Williamson ether synthesis?

Accepted Answer

$\mathrm{R-O^- + R'-X \xrightarrow{S_N2} R-O-R'}$

Question 13

Which of the following is a common solvent that is an ether?

Accepted Answer

Diethyl ether

Question 14

What is the product of the hydrolysis of an ether under acidic conditions?

Accepted Answer

Two alcohols

Question 15

Which of the following is true about the acid-catalyzed addition of alcohols to alkenes?

Accepted Answer

The reaction forms a carbocation intermediate.

Question 16

In the mechanism for acid-catalyzed ether formation, what is the first step?

Accepted Answer

Protonation of the alcohol by $\mathrm{H_2SO_4}$

Question 17

Which of the following is NOT a reason why ethers are often used as solvents?

Accepted Answer

They readily participate in acid-base reactions.

Question 18

Which of the following statements about the formation of ethers from alcohols and alkenes is correct?

Accepted Answer

The reaction is catalyzed by $\mathrm{H_2SO_4}$ and proceeds via a carbocation intermediate.

Question 19

Which of the following is a key feature of the mechanism for acid-catalyzed ether formation from alcohols?

Accepted Answer

The nucleophile is usually another alcohol molecule.

Ethers: Structure, Synthesis, and Mechanisms

Study Guide - Practice Questions